Wylder Hotel - Tilghman Island

Hotels
8.7 (228 reviews)
21551 Chesapeake House Drive , Tilghman Island , us

Free
Children allowed

Facilities

WiFi available
Free WiFi
Parking
Free Parking
Non-smoking rooms
Air conditioning
Swimming pool
Restaurant
Heating
Family rooms
See all facilities

Review Highlights

Pros:
Great location
Friendly staff
Lovely views
Cozy atmosphere
Cons:
Limited food service
Small room size
Cold food at buffet

Categories

Cleanliness
8.84
Clean and cute hotel room, standard quality for this hotel tier.
Service
9.31
Staff was kind and courteous, with special mentions of helpfulness.
Location
9.35
Beautiful property with stunning views, great location for a getaway.
Room Quality
7.8
Rooms are on the smaller side and have limited light blocking features.
Amenities
8.83
Lovely outdoor amenities, but less appealing in colder weather.
Value for Money
8.29
Good offerings, but resort fee seems high for provided amenities.
Food and Beverage
7.84
Food quality varies; buffet service issues mentioned, but generally good.
Overall Experience
9.31
Overall great experience, memorable stay with minor issues.
* This sentiment is summarized by AI based on user reviews.
Updated at: 2026-01-09 23:41

Property Description

Waterfront Charm and History
Experience the rebirth of a historic 1898 boarding house where watermen once ruled and crabs were a staple. The Wylder Hotel Tilghman Island pays homage to the hardworking fishermen of the past with a touch of irreverence, offering a welcoming vibe that instantly makes you feel at home.

Exciting Amenities
Indulge in the delights of Tickler’s Crab Shack & Restaurant and Bar Mumbo, or take advantage of the private marina with 25 boat slips. For adventure seekers, charter fishing trips and a variety of fun activities await. Whether you're an overnight guest or a local, there's something for everyone at this waterfront gem.

Eastern Shore Paradise
Escape to Tilghman Island, just a short drive from major cities like Baltimore, Washington D.C., and Philadelphia. Immerse yourself in the relaxed yet vibrant Eastern Shore lifestyle, filled with sailing, kayaking, and the freshest seafood. Book your stay now and discover the magic of Tilghman Island!

Important information:

The resort fee includes the following:

-Wifi

-Parking

-Paddleboards, Kayaks, Canoes

-Heated Saltwater Pool

-Fire Pits

-Lawn Games

-Woodfired Sauna

-Bicycles

- Continental breakfast served daily from 7:00-10:00

Please note that well-behaved dogs are permitted at this dog-friendly property. A nightly, per dog fee will be assessed. Contact property for details.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
Guests under the age of 18 can only check in with a parent or official guardian.
Managed by a private host
A deposit may be required at the property.

Check-in and check-out hours:
Check-out: 11:00 AM
Airport code: BWI

Location

Guest Reviews

8.7
Based on 228 reviews
Cleanliness: 8.84
Service: 9.31
Location: 9.35
Room Quality: 7.8
Amenities: 8.83
Value for Money: 8.29
Food and Beverage: 7.84
Overall Experience: 9.31
T
T262PRmichelleg Business
10
Unwind, relax, and recharge on a little slice of heaven on earth
Pros:

From the moment we arrived, we were greeted with exceptional hospitality by Ramon and Lauren! We needed a bit more room than the unit we originally booked and were graciously upgraded the next night to accommodate our needs by Ramon.. Ramon offered help with our luggage and checked in throughout our long weekend stay; always with a smile, while Lauren solved our television issue promptly. The grounds are very well maintained offering a serene place to relax and recharge. Everything from the bikes available to ride and explore, the sauna and cold plunge, relaxing poolside, and enjoying our morning coffee outside on the waterfront was exactly what our souls needed. We will definitely be back to stay!

2026-07-27 via Tripadvisor
S
sgK8062XZ Family
10
Anniversary Quick Getaway
Pros:

This place was exactly what we needed to celebrate our anniversary while traveling with our toddler. The value for money felt very reasonable given everything included. There were plenty of activities for the whole family—our toddler had a blast with the pool, kayaking, and canoeing! Our room was clean, quiet, and relaxing. What set the experience apart was the staff. They were so kind and accommodated an early check-in and late check-out for us. They even gifted us a bottle of wine to celebrate our anniversary! Thank you Ramon and team. We will be returning!

2026-07-27 via Tripadvisor
C
Connector33077450358 Family
8
Nice stay by the water
Pros:

We loved being next to the water, the fire pits with s’mores kits were a lot of fun. We really enjoyed how peaceful and quiet it is and the amenities like kayak, paddle boards, bikes, and the saltwater pool. The restaurant on site to dine by the water was also a plus! The room we had was a little small and could use a little updating but overall we enjoyed our stay.

2026-07-25 via Tripadvisor
K
ketchscott Couples Annapolis, Maryland
10
A Great Escape!!
Pros:

Fantastic experience exceeded our expectations, the entire property is so well managed and cared for, highly recommend for an escape to Tilghman Island. Excellent staff, spotless everywhere, housekeeping excellent.
Rooms well appointed and totally renovated just a few years ago.
We came by boat, no dock fee, 30amp service, water depth 4+feet. Decks are old but very sufficient.
Restaurant & bar do a great job, all good.
Staying here is like stepping back in time,
take a breath and enjoy!

2026-07-20 via Tripadvisor
J
jenniferlU190OA Family
10
Great stay
Pros:

Great atmosphere, pretty waterfront property. Kayaks, paddle boards and a great pool. Really friendly and professional staff, who make it like your staying with friends. Fantastic drinks, the bartender knows what he's doing for sure. the food and crab are perfect. This was our 2nd time and we will be back.

2026-07-20 via Tripadvisor
V
Vacation67526717585 Friends getaway
10
Thanks Isaiah!
Pros:

I probably wouldn’t have left a review but then I met Isaiah who was a total gem. Throughout the day he helped with everything we needed: water, towels, ice for the cold plunge, and starting one of the fire pits. Not only did was he efficient but he was such a delight. We really enjoyed chatting with him and were so impressed by his work ethic.

As others have mentioned the rooms leave a lot to be desired here. The service really made up for it.

2026-07-17 via Tripadvisor
C
cindymN547VF Family
10
Relax play and stay at Wydler Hotel Tilghman Island
Pros:

Wydler Hotel Tilghman Island is a true gem and offers a stay and play type of concept. The chesapeak bay sits on the property which adds to the relaxing type of vibes you get making for a pleasurable visit. The island itself is kept rural and is small with only a few added businesses. The country store is close enough to walk or why not take a bike which Wydler provides. 2 Vintage Chicks is another small business on the island and well worth checking out.
What makes Wydler Hotel extra special is all the extra attention the staff puts into making this a 5 star resort. I'd like to Thank the Front desk both Ashley and Lauren. I booked through Ashley and I appreciate her hospitality and kindness. Thank you Ashley for the recommending black walnut point for taking evening sunset pictures.
Thank you Lauren for welcoming us with a champagne toast stacking the wood and lighting the camp fires and our many chats. ( And thank you Ashley for the kind note you left Lauren regarding my booking)
Thank you to Ticklers Crab shack for getting us on a few early evenings when I forgot to make reservations. It was a pleasure to meet some of the servers as well as the greeter and manager. Thank you to Angie who was our server more then once. Angie even on a few busy evenings you made sure we were taken care of and we hardly had any waiting time. I will miss your smile. And thank you to Jeffery our amazing chef. The peeled shrimp was one of the best Ive had. Not only was it a large portion of shrimp but the old bay combined with fresh garlic made my taste buds come alive. The Ribs were also tender and I liked the way the bbq sauce was cooked into the meat.
And thank you Ticklers for providing the live music on Fathers day. My husband and I couldn't get enough of the solo guitar player and singer who played the best music. One song after another.
And last but far from least thank you housekeeping. Every day we enjoyed clean sheets towels and we lived having a clean room. The beds were extra comfortable.
Wydler hotel Tilghman island has a fb page as well as a instaghram one for you to check out and see all it has to offer. After meeting and chatting with more then a few guests it came as no surprise then most keep coming back. Some of the guests reported it was a 3rd visit. We will be back next year and were already missing the Wydler hotel experience. Thank you Wydler Hotel for an amazing trip filled with happy memories. We will see you next year!

2026-06-26 via Tripadvisor
K
Kyle couple us
10
2026-06-22 via Nuitee
J
Jacob couple us
9
Overall excellent staff, Very Clean comfortable setting. The price for what we had was dampened by the lack of food and
Pros:

Overall quiet, comfortable room. We had a partial view, and the overall layout of the property was very inviting. We also stayed a Sunday-Wed 3 night stay.

Cons:

The lack of dining options. I don’t know if it’s an all year thing or if we were a week early but the Wed-Sunday openings are most likely the reason people stay more towards the St. Michaels area. The opportunity is there, it just needs to be taken.

2026-06-18 via Nuitee
B
Bree solo_traveller us
10
Peaceful stay with a wonderful experience
Pros:

Friendly and welcoming staff

Cons:

No fridge in room

2026-06-17 via Nuitee
S
Sheila couple us
5
My stay was ok - I was disappointed with the cost of the room per night in relation to the quality.
Pros:

The facilities were nice and I am sure great fun with sunnier weather. I feel like the room charge was way overpriced even for a holiday weekend.

Cons:

I thought the room was small, no closet, tiny sink and outdated bathroom (for the price per night) The water smelt of sulfur and was hard to shower in. Room did not warrant the cost per night. The food was also not the caliber one would expect at this being called a resort and a again for the cost per/night.

2026-05-25 via Nuitee
J
Jesus couple us
9
Worth the stay.
Pros:

The views and environment

Cons:

The pillows

2026-05-08 via Nuitee
C
Compass45460204819 Family
10
Great weekend escape
Pros:

Stayed at Wylder Hotel Tilghman Island and loved the relaxed waterfront vibe. Beautiful sunsets, family-friendly atmosphere, and great outdoor amenities like bikes, kayaks, and fire pits.

2026-04-30 via Tripadvisor
G
Guy couple il
6
Cons:

Strong sulfur smell while in shower , you can't really enjoy taking a bath or a shower.
Rooms are super small and the Sink is a small one and inside the main room , not in the Bathroom.

2026-04-30 via Nuitee
E
emilygT8251KK Solo travel
8
Helpful staff!!
Pros:

Kind and very helpful staff!! We’re having a great time.

2026-04-21 via Tripadvisor
S
Stephen family_with_children us
9
2026-04-20 via Nuitee
Z
Z7496GXkristenj Friends getaway
10
This is how you do the bay
Pros:

When you first set eyes on the Wylder Hotel - with its pristine white sidings, contrasting dark shutters, and manicured lush trees - you’re all at once hit with that special feeling of coastal comfort, the kind only found in quaint, idyllic East Coast beach towns. Next, you walk through the cozy and welcoming check-in area and you meet Ramon - the attentive front desk supervisor who radiates warmth - and you automatically know you’re going to love your stay here. And finally, when you see the crown jewel of this hotel, its panoramic Bay side view, you realize that you never want to leave. My best friend and I decided to take an impromptu staycation at the Wylder Hotel and we couldn’t be more happy with our visit. There’s so much to experience at this gorgeous hotel. From the heated-salt outdoor pool to fun water adventure activities in the Bay to eating s’mores by the fire pits. Our stay at Wylder was brief, way too brief, literally-only-one-night-brief, but that was enough for us to already make plans to come back. Special shoutout to Ramon for providing us the best customer service, including helping us book another stay, fetching towels for us unprompted, and giving us recs for places to eat and visit. All we can say is that we love the Wylder!

2026-04-15 via Tripadvisor
4
448hermans Friends getaway
10
Just wow
Pros:

This was such a lovely experience.
Everyone there was very friendly.
Ramone was especially helpful and friendly.
I liked the fact they had free bicycles to ride around on and the view is spectacular.
They also have an outdoor sauna which you can enjoy while looking out over the bay.
I strongly encourage anyone who wants a relaxing weekend with plenty to do to go there.
The cornhole area was very well kept and for all you duffers out there they have a little driving range to use as well as some wiffle balls to smack out to a small receptacle.
I can’t say enough nice things about this place.
Just go ahead and make your reservations and enjoy yourself.

2026-04-13 via Tripadvisor
L
Lisa couple us
10
2026-04-12 via Nuitee
L
Landos couple us
10
2026-04-07 via Nuitee